Реакция #4778

Уравнение реакции

methyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate

hydrogen bromide acetic acid

→

methyl 6-bromomethyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate

Выход 66.4%

Растворители

acetic acid

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred for 10 minutes
2. 2
   ДругоеThe resulting precipitates
3. 3
   Другоеwere collected
4. 4
   workup.DISSOLUTIONdissolved in a mixture of chloroform (50 ml) and water (50 ml)
5. 5
   ПромывкаThe separated organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively
6. 6
   Сушкаdried over magnesium sulfate
7. 7
   ДругоеThe solvent was evaporated in vacuo
8. 8
   Другоеthe residual crystal was recrystallized from ethanol

Методика

A mixture of methyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (5 g), pyridinium bromide perbromide (5.6 g) and 25% hydrogen bromide-acetic acid (5 ml) in acetic acid (200 ml) was stirred for 2 hours at room temperature. The reaction mixture was poured into ice water (200 ml) and stirred for 10 minutes. The resulting precipitates were collected and dissolved in a mixture of chloroform (50 ml) and water (50 ml). The separated organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride successively, dried over magnesium sulfate. The solvent was evaporated in vacuo and the residual crystal was recrystallized from ethanol to give methyl 6-bromomethyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (4.07 g).

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